# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_as_513_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2173504'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N O2'
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_weight         237.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6245(10)
_cell_length_b                   11.4172(8)
_cell_length_c                   7.6696(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.208(3)
_cell_angle_gamma                90
_cell_volume                     1251.64(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1652 before and 0.1223 after correction. The Ratio of minimum to maximum transmission is 0.6038. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1438
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            65497
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1728
_reflns_number_total             2205
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.3326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66442(8) 0.58898(11) 0.21538(16) 0.0472(4) Uani 1 1 d . . . . .
O2 O 0.61417(10) 0.73473(13) 0.0241(2) 0.0629(4) Uani 1 1 d . . . . .
C1 C 0.50245(12) 0.62818(15) 0.1461(2) 0.0408(4) Uani 1 1 d . . . . .
N2 N 0.82264(14) 0.81204(18) 0.3121(3) 0.0720(6) Uani 1 1 d . . . . .
C0AA C 0.32270(15) 0.5786(2) 0.1818(3) 0.0630(6) Uani 1 1 d . . . . .
H0AA H 0.262118 0.562196 0.194239 0.076 Uiso 1 1 calc R . . . .
C2 C 0.33864(16) 0.6707(2) 0.0783(3) 0.0703(7) Uani 1 1 d . . . . .
H2 H 0.288800 0.716445 0.020312 0.084 Uiso 1 1 calc R . . . .
C3 C 0.42807(14) 0.69603(19) 0.0593(3) 0.0577(5) Uani 1 1 d . . . . .
H3 H 0.438523 0.758581 -0.011698 0.069 Uiso 1 1 calc R . . . .
C4 C 0.59667(13) 0.65819(16) 0.1194(2) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.75624(13) 0.60981(16) 0.1840(3) 0.0475(5) Uani 1 1 d . . . . .
H5 H 0.753202 0.609095 0.055088 0.057 Uiso 1 1 calc R . . . .
C6 C 0.82147(13) 0.51473(17) 0.2695(3) 0.0510(5) Uani 1 1 d . . . . .
C7 C 0.81234(17) 0.4620(2) 0.4255(4) 0.0786(7) Uani 1 1 d . . . . .
H7 H 0.763451 0.483172 0.479325 0.094 Uiso 1 1 calc R . . . .
C8 C 0.8755(2) 0.3777(3) 0.5026(5) 0.1004(10) Uani 1 1 d . . . . .
H8 H 0.868325 0.340556 0.606793 0.121 Uiso 1 1 calc R . . . .
C9 C 0.94885(19) 0.3486(2) 0.4258(5) 0.0963(10) Uani 1 1 d . . . . .
H9 H 0.991893 0.292343 0.478582 0.116 Uiso 1 1 calc R . . . .
C10 C 0.39564(15) 0.51050(19) 0.2674(3) 0.0575(5) Uani 1 1 d . . . . .
H10 H 0.384484 0.447828 0.337536 0.069 Uiso 1 1 calc R . . . .
C11 C 0.48559(14) 0.53486(17) 0.2496(2) 0.0483(5) Uani 1 1 d . . . . .
H11 H 0.535003 0.488380 0.307454 0.058 Uiso 1 1 calc R . . . .
C12 C 0.79108(14) 0.72508(19) 0.2561(3) 0.0528(5) Uani 1 1 d . . . . .
C13 C 0.89492(16) 0.4842(2) 0.1933(4) 0.0763(7) Uani 1 1 d . . . . .
H13 H 0.901691 0.519368 0.087370 0.092 Uiso 1 1 calc R . . . .
C14 C 0.95866(19) 0.4015(3) 0.2738(5) 0.0975(10) Uani 1 1 d . . . . .
H14 H 1.008889 0.381914 0.222653 0.117 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.356(2) . ?
O1 C5 1.434(2) . ?
O2 C4 1.201(2) . ?
C1 C3 1.386(3) . ?
C1 C4 1.475(3) . ?
C1 C11 1.382(3) . ?
N2 C12 1.140(3) . ?
C0AA H0AA 0.9300 . ?
C0AA C2 1.366(3) . ?
C0AA C10 1.370(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C5 H5 0.9800 . ?
C5 C6 1.501(3) . ?
C5 C12 1.476(3) . ?
C6 C7 1.371(3) . ?
C6 C13 1.372(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(4) . ?
C9 H9 0.9300 . ?
C9 C14 1.347(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.378(4) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 114.51(14) . . ?
C3 C1 C4 117.70(17) . . ?
C11 C1 C3 119.32(18) . . ?
C11 C1 C4 122.96(16) . . ?
C2 C0AA H0AA 119.9 . . ?
C2 C0AA C10 120.2(2) . . ?
C10 C0AA H0AA 119.9 . . ?
C0AA C2 H2 119.8 . . ?
C0AA C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C3 H3 120.1 . . ?
C2 C3 C1 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
O1 C4 C1 112.70(15) . . ?
O2 C4 O1 121.94(17) . . ?
O2 C4 C1 125.37(17) . . ?
O1 C5 H5 108.9 . . ?
O1 C5 C6 109.75(15) . . ?
O1 C5 C12 110.27(14) . . ?
C6 C5 H5 108.9 . . ?
C12 C5 H5 108.9 . . ?
C12 C5 C6 110.12(16) . . ?
C7 C6 C5 121.91(18) . . ?
C7 C6 C13 119.3(2) . . ?
C13 C6 C5 118.7(2) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C14 C9 C8 120.0(3) . . ?
C14 C9 H9 120.0 . . ?
C0AA C10 H10 120.0 . . ?
C0AA C10 C11 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C1 C11 H11 119.9 . . ?
C10 C11 C1 120.14(18) . . ?
C10 C11 H11 119.9 . . ?
N2 C12 C5 176.4(2) . . ?
C6 C13 H13 120.0 . . ?
C6 C13 C14 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.6(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C7 -33.6(3) . . . . ?
O1 C5 C6 C13 149.71(19) . . . . ?
C0AA C2 C3 C1 -0.2(3) . . . . ?
C0AA C10 C11 C1 0.2(3) . . . . ?
C2 C0AA C10 C11 0.2(3) . . . . ?
C3 C1 C4 O1 177.76(16) . . . . ?
C3 C1 C4 O2 -2.3(3) . . . . ?
C3 C1 C11 C10 -0.6(3) . . . . ?
C4 O1 C5 C6 -169.47(14) . . . . ?
C4 O1 C5 C12 69.05(19) . . . . ?
C4 C1 C3 C2 179.25(19) . . . . ?
C4 C1 C11 C10 -179.17(17) . . . . ?
C5 O1 C4 O2 -4.0(2) . . . . ?
C5 O1 C4 C1 175.90(14) . . . . ?
C5 C6 C7 C8 -177.9(2) . . . . ?
C5 C6 C13 C14 176.7(2) . . . . ?
C6 C7 C8 C9 1.6(5) . . . . ?
C6 C13 C14 C9 1.0(4) . . . . ?
C7 C6 C13 C14 -0.1(4) . . . . ?
C7 C8 C9 C14 -0.7(5) . . . . ?
C8 C9 C14 C13 -0.6(5) . . . . ?
C10 C0AA C2 C3 -0.2(3) . . . . ?
C11 C1 C3 C2 0.6(3) . . . . ?
C11 C1 C4 O1 -3.7(2) . . . . ?
C11 C1 C4 O2 176.23(18) . . . . ?
C12 C5 C6 C7 88.0(2) . . . . ?
C12 C5 C6 C13 -88.7(2) . . . . ?
C13 C6 C7 C8 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
